HK1083860A - Two-component silylated polyurethane adhesive, sealant and coating compositions - Google Patents

Description

Two-component silylated polyurethane adhesives, sealants and coating compositions

Background

1. Field of the invention

The present invention relates to two-component adhesive, sealant and coating compositions, and in particular to two-component compositions containing silylated polyurethane.

2. Background of the invention

Adhesives are commonly used to join or secure two or more adherends. A bond is considered to be any two or more materials or pieces of materials joined together, including wood, metal, plastic, paper, ceramic, stone, glass, concrete, and the like. Adhesives for these purposes are based on a variety of technologies including elastomer/solvent/resin mixtures, epoxies, latexes, polyurethanes, silicones, cyanoacrylates, acrylics, hot melts, and the like. These adhesives have one or more disadvantages, for example, they may contain toxic and often flammable solvents, they may be incompatible with one or more types of adherends, they may have undesirably long cure times, and in many cases, the strength of the joint they form is inadequate.

It is often desirable to provide a desired appearance to a coating applied to a substrate, and in many cases, a multi-layer coating approach is used, the last of which may be a pigmented or unpigmented surface layer. Unfortunately, as the article containing the coated substrate ages, normal "wear and tear" induced scratches will tend to detract from the appearance of the coated surface of the substrate.

The sealant is typically a film, often comprising plastic, that is coated onto one or more surfaces of one or more substrates to prevent the passage of gases or liquids through the film. Sealants can be used to prevent exposure of the substrate or, more often, through defects in the substrate or gaps between substrates.

Silane functional resins are typically cured or crosslinked in two steps, requiring first the reaction of water with an alkoxysilane group to form a silanol group, and then reacting the silanol group with another silanol group or an alkoxysilane. In the formulation of one-component silanes, catalysts are usually added to increase the reaction rate. In many cases, water absorption is a limiting step in the curing or crosslinking process.

Us patent 5,936,032 to Angus, jr discloses a two-part room temperature vulcanizable silicone adhesive sealant composition consisting of components a and B. Component A comprises an alkoxy-terminated polydiorganosiloxane, a condensation cure catalyst, and a polyalkoxysilane crosslinking agent. Component B comprises water and a disilanol-terminated polydiorganosiloxane.

U.S. patents 4,386,992 and 4,379,840 to Takegawa et al disclose a two-part adhesive comprising an aqueous synthetic resin emulsion adhesive and a gelling agent comprising a calcium salt, which may be calcium aspartate, and a combination of an organic or inorganic acid salt.

U.S. Pat. No. 6,649,016 to Wu et al discloses an adhesive composition for bonding glass to a painted substrate, the composition comprising one or more polymers having a flexible backbone and silane moieties capable of silanol condensation; one or more titanates or zirconates; and anhydrous strong organic acids.

Morikawa et al, U.S. published application 20030055197A1, discloses a laminate adhesive comprising a polyisocyanate curing agent containing an isocyanate-terminated prepolymer and a silane coupling agent, and an active hydrogen-containing resin.

U.S. patent 6,114,436 to Roesler discloses moisture curable compositions containing a polyisocyanate having (cyclo) aliphatically bonded isocyanate groups, and a compound containing alkoxysilane groups. These moisture-curable compositions are useful in coatings, adhesives or sealants.

U.S. patent 6,096,823 to Shaffer discloses moisture curable compounds containing isocyanate groups and alkoxysilane groups, and optionally containing repeating ethylene oxide units. The alkoxysilane groups are introduced as the reaction product of a polyisocyanate component and an amino compound containing alkoxysilane groups. These moisture-curable compositions are useful in adhesives or as sealing compositions for adhesives.

U.S. Pat. No. 5,554,709 to Emmerling et al discloses moisture curable alkoxysilane terminated polyurethanes obtained by reacting polyurethane prepolymers with sulfur-free alkoxysilanes. The moisture curable alkoxysilane terminated polyurethanes are useful in sealing and/or adhesive compositions.

However, known adhesives, sealants, and coatings using silane functional resins have poor or short shelf life and/or stability, and/or slow cure speeds. Thus, it is desirable that adhesives containing silane functional resins have excellent or long shelf life and reasonably fast cure or crosslinking speed.

Summary of The Invention

The present invention relates to two-component adhesive, sealant and/or coating compositions comprising (i) a first component comprising a portion of alkoxysilane-functional urethane and water, and (ii) a second component comprising the remaining portion of alkoxysilane-functional urethane and a catalyst. The alkoxysilane-functional urethane includes the reaction product of a) and b) below

a) A reaction product of a hydroxy-functional compound and a polyisocyanate, the reaction product containing isocyanate functional groups; and

b) a compound of formula I:

wherein the content of the first and second substances,

x represents the same or different and is selected from C₁-C₁₀Straight or branched alkyl and C₁-C₁₀With the proviso that at least two X are alkoxy groups and if one or both X groups are methoxy groups, at least one X group must be C₁-C₁₀A linear or branched alkyl group,

y represents C₁-C₈A linear or branched alkylene group, which may be substituted,

R₂and R₅Are identical or different and represent organic radicals which are inert to isocyanate groups at temperatures of 100 ℃ or less, and

R₃and R₄Are identical or different and represent hydrogen or an organic group which is inert towards isocyanate groups at temperatures of 100 ℃ or less.

The invention also relates to a process for applying the two-component composition described above, comprising mixing component (i) and component (ii). Embodiments of the invention relate to applying the mixture to one or more substrates.

The invention also relates to a method of bonding a first substrate to a second substrate. The method comprises (a) combining component (i) and component (ii) to form a mixture, applying a coating of the mixture to at least one surface of a first substrate or a second substrate, and contacting one surface of the first substrate with one surface of the second substrate, wherein at least one contacting surface has the coating applied thereto.

The invention also relates to an assembly, prepared according to the above method, comprising at least a first substrate and a second substrate bonded together.

The present invention also provides a method of coating a substrate comprising applying the two-component composition described above to at least a portion of the surface of a substrate, and a substrate prepared according to the method.

Detailed Description

Other than in the operating examples, or where otherwise indicated, all numbers or expressions referring to quantities of ingredients used in the specification and claims, reaction conditions, and so forth, may be understood as modified in all instances by the word "about". The present patent application discloses different numerical ranges. Because these ranges are continuous, they include any value between the minimum and maximum values. Except where expressly indicated, the various numerical ranges specified in this application are approximations.

The term "alkyl" as used herein refers to a group of formula C_sH_2s+1Wherein "s" is the specified number of carbon atoms or a range thereof. The term "substituted alkyl" refers to alkyl groups in which one or more hydrogen atoms are replaced with a non-carbon atom or group, non-limiting examples of which include halogens, amines, alcohols, oxygen (e.g., ketone or aldehyde groups), and thiols.

The term "cyclic alkyl" or "cycloalkyl" as used herein means to form a compound of the formula C_sH_2s-1Wherein "s" is the specified number of carbon atoms or a range thereof. The term "substituted cycloalkyl" refers to a cycloalkyl group containing one or more heteroatoms in the cyclic structure, and/or one or more hydrogen atoms replaced with non-carbon atoms or groups, wherein non-limiting examples of heteroatoms are-O-, -NR-, and-S-, and non-limiting examples of non-carbon atoms or groups include halogens, amines, alcohols, oxygen (e.g., ketone or aldehyde groups), and thiols. "R" represents an alkyl group having 1 to 24 carbon atoms.

The term "aryl" as used herein refers to a monovalent group of an aromatic hydrocarbon. The aromatic hydrocarbons include those cyclic compounds containing conjugated double bonds based on carbon atoms, in which 4t +2 electrons are contained in the resulting cyclic conjugated pi-orbital system, t being an integer of at least 1. Aryl groups, as used herein, include single aromatic ring structures, one or more fused aromatic ring structures, covalently linked aromatic ring structures, any or all of which may include heteroatoms. Non-limiting examples of these heteroatoms that may be included in the aromatic ring structure include O, N, and S.

The term "alkylene" as used herein refers to a carbon chain length of from C₁(in the case of acyclic) or C₄(in the case of cyclic) to C₂₅Especially from C₂To C₁₂The divalent hydrocarbon of (1) may be substituted or unsubstituted, and may contain a substituent. As a non-limiting example, the alkyleneThe group may be a lower alkyl group having 1 to 12 carbon atoms. As a non-limiting example, "propylene" includes n-propylene and isopropylene; likewise, "butylene" includes n-butylene, isobutylene, and t-butylene.

As used herein, the terms "(meth) acrylic acid" and "(meth) acrylate" are meant to include the corresponding derivatives of acrylic acid and methacrylic acid, without limitation.

As used herein, the term "cure" is intended to include crosslinking of the adhesive, sealant, or coating composition components and film formation resulting from the evaporation of water and, if present, other solvents and diluents, with concomitant increase in the physical and chemical properties of the resulting film, such as bond strength and peel strength.

The term "crosslinking" as used herein refers to the formation of short side chains in a molecule that links two longer molecular chains together by reaction between two or more functional groups on the short side chains.

Embodiments of the present invention provide a two-part adhesive, sealant, and/or coating composition comprising an alkoxysilane-functional urethane comprising the reaction product of a) and b) below

a) An isocyanate functional group-containing reaction product of a hydroxy functional compound and a polyisocyanate; and

b) a compound represented by formula I (amine functional aspartate):

wherein the content of the first and second substances,

x represents the same or different and is selected from C₁-C₁₀Straight or branched alkyl and C₁-C₁₀Straight or branched alkoxy, with the proviso that at least two X are alkoxy and, if one or both X groups are methoxy, toAt least one X group must be C₁-C₁₀A linear or branched alkyl group,

y represents C₁-C₈A linear or branched alkylene group, which may be substituted,

R₂and R₅Are identical or different and represent organic radicals which are inert to isocyanate groups at temperatures of 100 ℃ or less, and

R₃and R₄Are identical or different and represent hydrogen or an organic group which is inert towards isocyanate groups at temperatures of 100 ℃ or less.

Because some silane functional resins and water are observed to react very rapidly, water-based adhesives, sealants, and coatings prepared using silane functional resins can create problems that preclude their use in water-based adhesive, sealant, and coating compositions. For example, trimethoxysilane functional resins (that is, when all three X groups in formula I are methoxy) are such as to react with water such that they cannot be used in the preparation of water-based adhesives, sealants and coating compositions. As described herein, the reactivity of the silane groups can be controlled by the selection of the higher alkoxysilane substituents and, optionally, the alkyl substituents.

Referring to formula I, when one of the X groups is an alkoxy group, even if the other two X groups are methoxy groups, the reaction rate between the silane groups and water will be reduced to the extent that the formulation of the silane-functional resin in water-based adhesive, sealant and coating compositions becomes possible. In addition, when all three X groups are C₂-C₁₀With alkoxy groups, the reaction rate between the silane groups and water will be reduced to the extent that the formulation of the silane-functional resin in water-based adhesive, sealant and coating compositions becomes possible.

When formulated in a two-component system in which one component is free of water and contains a suitable catalyst, the silane-functional resin has a reasonably fast cure or crosslinking speed once mixed. Thus, a very useful adhesive, sealant and/or coating composition is provided.

In one embodiment of the invention, any suitable hydroxy compound may be used in a). Non-limiting examples of suitable hydroxy-functional compounds include monohydric alcohols, dihydric alcohols, polyhydric alcohols, and mixtures thereof. Other non-limiting examples of suitable hydroxyl-functional compounds include polyester monols, diols, polyols and mixtures thereof, (meth) acrylic monols, diols, polyols and mixtures thereof, polyether monols, diols, polyols and mixtures thereof, hydrocarbon monols, diols, polyols and mixtures thereof.

When polyether monols, diols, and polyols are used, the polyether has a number average molecular weight of at least 250, in some cases at least 500, and in other cases at least 1,000. Furthermore, the number average molecular weight of the compounds of formula I can be up to 20,000, in some cases up to 15,000, and in other cases up to 12,000. The number average molecular weight of the compound of formula I may be arbitrarily changed within the above numerical range.

The number average molecular weight can be determined by titration and/or gel permeation chromatography using appropriate standards.

Any suitable polyether monol, diol, and/or polyol may be used in the present invention. Suitable processes for preparing polyethers are known and include the KOH process known from the prior art and those described in detail, for example in EP-A283148 and U.S. Pat. Nos. 3,278,457, 3,427,256, 3,829,505, 4,472,560, 3,278,458, 3,427,334, 3,941,849, 4,721,818, 3,278,459, 3,427,335 and 4,355,188.

In one embodiment of the present invention, the polyethers used in the present invention may contain unsaturated groups.

In another embodiment of the invention, the polyethers have a maximum total degree of unsaturation of 0.1 milliequivalents per gram (meq/g) or less, in some cases less than 0.04(meq/g), in other cases less than 0.02meq/g, in some cases less than 0.01meq/g, in other cases 0.007meq/g or less, and in particular cases 0.005meq/g or less. The amount of unsaturation is determined by the method of preparing the polyether and the molecular weight of the polyether. These polyethers are known and can be prepared by, as a non-limiting example, ethoxylation and/or propoxylation of suitable starter molecules. Non-limiting examples of suitable starter molecules include glycols such as ethylene glycol, propylene glycol, 1, 3-butanediol, 1, 4-butanediol, 1, 6-hexanediol, and 2-ethylhexanediol-1, 3. Suitable starter molecules may also be polyethylene glycol and polypropylene glycol.

Suitable polyester mono-, di-, and polyols are known in the art and are typically prepared by condensation of diols and/or polyols with dicarboxylic acids or esterifiable or transesterifiable dicarboxylic acid derivatives such as lower alkyl alcohol esters or acid chlorides. Examples of useful diols and polyols include ethylene glycol, 1, 2-and 1, 3-propanediol, 1, 4-butanediol, 1, 6-hexanediol, cyclohexanedimethanol, 1, 4-cyclohexanediol, glycerol, and the like. Suitable carboxylic acids or their derivatives include 1, 4-succinic acid, glutaric acid, adipic acid, adipoyl dichloride, azelaic acid, phthalic acid, isophthalic acid, terephthalic acid, dimethyl terephthalate, and the like. Generally, to minimize viscosity, only a minimal amount of trifunctional or higher functional monomers is used.

The polyester mono-, di-, and poly-ols have a number average molecular weight in the range of 500-15,000, in some cases 1,000-8,000, and in other cases 2,000-6,000, and will be higher in each range if a tri-or tetra-alcohol is used.

Suitable (meth) acrylic mono-, di-, and poly-alcohols include homopolymers and copolymers of hydroxy-functional (meth) acrylic monomers prepared by known polymerization methods. Suitable hydroxy-functional (meth) acrylic monomers that can be used include, but are not limited to, hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, and hydroxy-functional polyethers prepared by reacting hydroxyethyl (meth) acrylate or hydroxypropyl (meth) acrylate with ethylene oxide and/or propylene oxide.

The mono-, di-and poly (meth) acrylic acid alcohols have a number average molecular weight in the range of 500-15,000, in some cases 1,000-8,000 and in other cases 2,000-6,000.

Suitable hydrocarbon mono-, di-, and polyols include, but are not limited to, C₂-C₂₀Linear, branched and cyclic alkyl, aryl, alkaryl and aralkyl mono-, di-and polyhydric alcohols, ethylene glycol, 1, 2-and 1, 3-propanediol, 1, 4-butanediol, 1, 6-hexanediol, cyclohexanedimethanol, 1, 4-cyclohexanediol, glycerol and the like, polybutadiene diols and their hydrogenated counterparts, and mixtures thereof.

In one embodiment of the present invention, any suitable polyisocyanate may be used for a). In certain embodiments of the present invention, the polyisocyanate contains two or more, and in some cases 2 to 6, isocyanate groups. In a particular embodiment of the invention, the polyisocyanate has the structure shown in formula (III):

OCN-R⁷-NCO (III)

wherein R is⁷Is selected from C₂-C₂₄Linear, branched and cyclic alkylene, arylene and aralkylene groups, which may optionally contain one or more isocyanate groups.

In a further specific embodiment, the polyisocyanate is selected from the group consisting of 1, 4-diisocyanatobutane, 1, 5-diisocyanatopentane, 1, 6-diisocyanatohexane, 2-methyl-1, 5-diisocyanatopentane, 1, 5-diisocyanato-2, 2-dimethylpentane, 2, 4-trimethyl-1, 6-diisocyanatohexane, 2, 4, 4-trimethyl-1, 6-diisocyanatohexane, 1, 10-diisocyanatodecane, 1, 3-diisocyanatocyclohexane, 1, 4-diisocyanatocyclohexane, 1, 3-bis- (isocyanatomethyl) cyclohexane, 1, 4-bis- (isocyanatomethyl) cyclohexane, 1, 5-diisocyanatopentane, 1, 2-dimethylene, 2, 4-trimethyl-diisocyanatohexane, 1, isophorone diisocyanate, 4 ' -diisocyanatodicyclohexylmethane, triisocyanatononane, omega ' -diisocyanato-1, 3-dimethylcyclohexane, 1-isocyanato-1-methyl-3-isocyanatomethylcyclohexane, 1-isocyanato-1-methyl-4-isocyanatomethylcyclohexane, bis- (isocyanatomethyl) norbornane, 1, 5-naphthalene diisocyanate, 1, 3-bis- (2-isocyanatoprop-2-yl) benzene, 1, 4-bis- (2-isocyanatoprop-2-yl) benzene, 2, 4-diisocyanatotoluene, 2, 6-diisocyanatotoluene, 2-diisocyanatotoluene, triisocyanatononane, omega ' -diisocyanato-1, 3-diisocyanato-1-methyl-3-isocyanatomethylcyclohexane, 1-isocyanato-1-methyl-4-isocyanatomethylcyclohexane, bis- (, 2, 4 '-diisocyanatodiphenylmethane, 4' -diisocyanatodiphenylmethane, 1, 5-diisocyanatonaphthalene, 1, 3-bis (diisocyanatomethyl) benzene and mixtures thereof.

In another particular embodiment, the polyisocyanate includes a conventional polyisocyanate selected from biurets, uretdiones ("dimers"), allophanates and isocyanurates containing one or more other isocyanate groups, and iminooxadiazinediones ("trimers") of suitable isocyanate-functional compounds are useful in the present invention.

In one embodiment of the present invention, polyisocyanates having a functionality greater than 2 may be used. Suitable examples of polyisocyanates having a functionality greater than 2 include, but are not limited to, isocyanurates, biurets, uretdiones, and allophanates. Isocyanurates may be formed by trimerization of aliphatic or aromatic diisocyanates, as is known in the art.

Biurets can be formed by adding a small amount of water to two moles of isocyanate and reacting in the presence of a catalyst at elevated temperatures. Uretdiones can be formed by dimerization of isocyanates. Allophanates can be prepared by reacting a diisocyanate with a urethane binder.

In a particular embodiment of the present invention, the diisocyanates employed in the above-described syntheses of isocyanurates, biurets and uretdiones for use in the present invention include the commonly used aliphatic and aromatic diisocyanates, non-limiting examples of which include 1, 4-tetramethylene 1Hexamethylene diisocyanate, 1, 6-Hexamethylene Diisocyanate (HDI), 2, 4-trimethyl-1, 6-hexamethylene diisocyanate, 1, 12-dodecamethylene diisocyanate, 1-isocyanato-3-isocyanatomethyl-3, 5, 5-trimethyl-cyclohexane (isophorone diisocyanate or IPDI), tetramethylxylylene diisocyanate (TMXDI), bis- (4-isocyanatocyclohexyl) methane (H)₁₂MDI), bis (4-isocyanato-3-methyl-cyclohexyl) methane, Toluene Diisocyanate (TDI), bis (4-isocyanatophenyl) Methane (MDI), and mixtures thereof. Other non-limiting examples include the adduct of 3 moles of toluene diisocyanate to 1 mole of trimethylolpropane, the isocyanurate trimer of 1, 6-diisocyanatohexane, the isocyanurate trimer of isophorone diisocyanate, the uretdione dimer of 1, 6-diisocyanatohexane, the biuret trimer of 1, 6-diisocyanatohexane, the allophanate-modified trimer or higher oligomers of 1, 6-diisocyanatohexane, the adduct of 3 moles of m-alpha, alpha' -tetramethylxylene diisocyanate to 1 mole of trimethylolpropane, and mixtures thereof.

In one embodiment of the invention, the equivalent ratio of hydroxyl groups in the hydroxyl functional compound in a to isocyanate groups in the polyisocyanate is from 1: 10 to 1: 1, in some cases from 1: 5 to 1: 1, in other cases from 1: 5 to 1: 1.1, and in some cases from 1: 3 to 1: 1.25. a) The ratio of equivalents of the radicals in (a) is such that the reaction product in a) contains isocyanate functional groups.

In one embodiment of the invention, the reaction product of a) is reacted with an amine-functional aspartate compound b) corresponding to formula I. In a particular embodiment, the reaction of a) with b) causes the reactive silane groups corresponding to the compounds of formula I to be introduced into the alkoxysilane-functional carbamate by reaction of the isocyanate groups with the-NH-groups of formula I.

In one embodiment of the invention, the compounds corresponding to formula I comprise methyl, ethyl or C₃-C₂₀Linear, branched and cyclic alkyl, aryl,Alkylaryl and arylalkyl as radicals R which may be identical or different₂、R₅、R₃And R₄。

In one embodiment of the invention, the amino-functional aspartate corresponding to formula I is the reaction product of an N- (trialkoxysilylalkyl) amine with a dialkyl maleate. In a particular embodiment, the N- (trialkoxysilylalkyl) amine has a structure according to formula (II):

NH₂-R¹-Si(-O-R⁶)₃ (II)

wherein R is¹Is C₁-C₈A linear or branched alkylene group; r⁶Independently selected from C₂-C₁₀Straight or branched chain alkyl. In a particular embodiment, the N- (trialkoxysilylalkyl) is an N- (-3-trialkoxysilyl) amine.

In one embodiment of the invention, the reaction product of a) comprises at least 50, in some cases at least 55, in other cases at least 60, in some situations at least 65, and in other situations at least 70 weight percent of the alkoxysilane functional carbamate. Likewise, the reaction product of a) constitutes up to 99 weight percent, in some cases up to 97.5 weight percent, in other cases at least 90 weight percent, in some cases at least 85 weight percent, and in other cases at least 80 weight percent of the alkoxysilane functional carbamate. a) The reaction product of (a) may be present in the alkoxysilane-functional urethane at any of the levels described above, and may vary between any of the levels described above.

In one embodiment of the invention, the amine functional aspartate b) makes up at least 1 weight percent, in some cases at least 2.5 weight percent, in other cases at least 10 weight percent, in some cases at least 15 weight percent, and in other cases at least 20 weight percent of the alkoxysilane functional carbamate. Likewise, the amine functional aspartate can comprise up to 50 weight percent, in some cases up to 45 weight percent, in other cases at least 40 weight percent, in some situations at least 35 weight percent, and in other situations at least 30 weight percent of the alkoxysilane functional carbamate. The amine functional aspartic acid can be present in the alkoxysilane functional urethane at any of the levels described above, and can vary between any of the levels described above.

According to the invention, the isocyanate groups in a) react with the amine groups in b) to form at least initially urea groups. The urea groups initially formed can be converted into hydantoin groups in a known manner, for example, by heating the compound at elevated temperature, optionally in the presence of a catalyst. Hydantoin groups may also be formed over time under ambient conditions. Thus, the term "urea group" also includes other compounds containing a N-CO-N group, such as a hydantoin group.

In one embodiment of the present invention, a two-component adhesive, sealant and/or coating composition comprises:

(i) a first component comprising a portion of an alkoxysilane-functional urethane and water; and

(ii) a second component comprising a remaining portion of the alkoxysilane-functional urethane and a catalyst.

In one embodiment of the invention, catalysts useful in ii) include, but are not limited to, titanates, such as tetrabutyl titanate and tetrapropyl titanate; organic compounds such as dibutyltin dilaurate, dibutyltin maleate, dibutyltin diacetate, tin octylate and tin naphthenate; lead octoate; amine-based compounds and salts and carboxylates of these compounds, for example, butylamine, octylamine, dibutylamine, monoethanolamine, diethanolamine, triethanolamine, diethylenetriamine, triethylenetetramine, oleylamine, octylamine, cyclohexylamine, benzylamine, diethylaminopropylamine, xylylenediamine, triethylenediamine, guanidine, diphenylguanidine, 2, 4, 6-tris (dimethylaminomethyl) phenol, morpholine, N-methylmorpholine and 1, 3-diazabicyclo (5, 4, 6) undecene-7 (DBU); a low molecular weight polyamide resin prepared by reacting an excess of polyamine with a polybasic acid; the reaction product of an excess of polyamine and an epoxy compound; and known silanol condensing catalysts, for example, amino group-containing silane coupling agents (e.g., γ -aminopropyltrimethoxysilane and N- (. beta. -aminoethyl) aminopropylmethyldimethoxysilane). These compounds may be used alone or in combination.

In a particular embodiment, the catalyst in ii) is one or more selected from the group consisting of p-toluenesulfonic acid, dibutyltin dilaurate, dibutyltin acetylacetonate, triethylamine and triethylenediamine.

In one embodiment of the invention, the alkoxysilane functional urethane is present in an amount of at least 25 weight percent, in some cases at least 30 weight percent, and in other cases at least 35 weight percent of the first component. Likewise, the alkoxysilane functional urethane content is up to 75 weight percent, in some cases up to 70 weight percent, and in other cases up to 65 weight percent of the first component. The alkoxysilane functional carbamate can be present in the first component at any of the levels described above, and can vary between any of the levels described above.

In one embodiment of the invention, the amount of alkoxysilane functional urethane is at least 25 wt%, in some cases at least 30 wt%, and in other cases at least 35 wt% of the second component. Likewise, the amount of alkoxysilane functional urethane is up to 75 weight percent, in some cases up to 70 weight percent, and in other cases up to 65 weight percent of the second component. The alkoxysilane functional carbamate may be present in the second component at any of the levels described above, and may vary between any of the levels described above.

In one embodiment of the invention, the amount of alkoxysilane functional urethane is at least 25 weight percent, in some cases at least 30 weight percent, and in other cases at least 35 weight percent of the two-part composition. When the amount of alkoxysilane carbamate is too low, curing will be incomplete. Likewise, the amount of alkoxysilane-functional urethane may be up to 75 weight percent, in some cases up to 70 weight percent, and in other cases up to 65 weight percent of the two-part composition. When the amount of alkoxysilane carbamate is too high, the viscosity of the components becomes too high and the amount of pigment becomes insufficient, thereby limiting the tensile strength of the cured composition. The alkoxysilane functional carbamate may be present in the second component at any of the levels described above, and may vary between any of the levels described above.

In one embodiment of the invention, component i) is present in an amount of at least 10 wt%, in some cases at least 15 wt%, in other cases at least 20 wt%, in some cases at least 25 wt%, in other cases at least 30 wt% of the two-component composition. Likewise, the amount of component i) is up to 90, in some cases up to 85, in other cases up to 80, in some situations up to 75, and in other situations up to 70 weight percent of the two-component composition. Component i) may be present in the two-component composition at any of the levels described above and may vary between any of the levels described above.

In one embodiment of the invention, component ii) is present in an amount of at least 10 wt%, in some cases at least 15 wt%, in other cases at least 20 wt%, in some cases at least 25 wt%, in other cases at least 30 wt% of the two-component composition. Likewise, the amount of component ii) is up to 90, in some cases up to 85, in other cases up to 80, in some situations up to 75, and in other situations up to 70 weight percent of the two-component composition. Component ii) may be present in the two-component composition at any of the levels described above, and may vary between any of the levels described above.

In one embodiment of the invention, either the first component i) or the second component ii) may comprise one or more materials selected from leveling agents, wetting agents, flow control agents, anti-skinning agents, anti-foaming agents, fillers, adhesion promoters, viscosity modifiers, plasticizers, pigments, dyes, UV absorbers, thermal stabilizers, antioxidants and mixtures thereof.

Non-limiting examples of plasticizers useful in the present invention include dioctyl phthalate (DOP); dibutyl phthalate (DBP); diisodecyl Phthalate (DIDP); dioctyl adipate; isodecyl malonate; diethylene glycol dibenzoate, pentaerythritol esters; butyl oleate, methyl acetylricinoleate; tri (tolyl) phosphate and trioctyl phosphate; polypropylene glycol adipate, polybutylene glycol adipate, and the like. These plasticizers may be used alone or in combination of two or more. When plasticizers are used, they can control or achieve a desired viscosity of the first component, the second component, and/or the starting mixture of the first component and the second component.

Non-limiting examples of adhesion promoters useful in the present invention include epoxy resins, phenolic resins, silanes and aminosilane coupling agents known in the art, alkyl titanates and/or aromatic polyisocyanates.

Non-limiting examples of leveling agents useful in the present invention include cellulose, e.g., nitrocellulose and cellulose acetate butyrate.

Non-limiting examples of wetting agents that can be used in the present invention include glycols, silanes, anionic surfactants, and any other wetting agent known in the art.

Non-limiting examples of flow control agents useful in the present invention include polyacrylates, nonionic fluorinated alkyl ester surfactants, nonionic alkylaryl polyether alcohols, silicones, and the like, and those sold under the trade name RESIFLOW by Estron chemical, Inc., Parsiplay, N.J.^*And BENZOIN, tradename of DSM, Inc^*And the product name of the product from Monsanto is MODAFLOW^*And sold under the trade name SURFYNOL by air products, Bethlehem, Pa^*The product of (1).

Non-limiting examples of antiskinning agents useful in the present invention include lecithin, oximes, non-limiting examples being butyraldehyde oxime and methyl ethyl ketoxime, hydroquinone, non-limiting examples being 2, 5-di-t-butylhydroquinone and the methyl esters of hydroquinone with anthraquinone.

Non-limiting examples of antifoamants useful in the present invention include those available from PhiladelThe trade name FOAMEX of phia, PA, Rohm and Haas^*Those available under the trade name BYK from BYK-ChemieUSA, Wallingford, CT^*And those available under the trade name Foam Brake from BASF Corp^*The product of (1).

Non-limiting examples of fillers useful in the present invention include fumed silica, precipitated silica, silicic anhydride, hydrated silicic acid (silicic hydrate), talc, carbon black, limestone powder, coated and uncoated colloidal calcium carbonate, coated and uncoated ground calcium carbonate, coated and uncoated precipitated calcium carbonate, kaolin, diatomaceous earth, sintered clay, titanium dioxide, bentonite, organobentonite, ferric oxide, zinc oxide, activated zinc white, and fibrous fillers such as glass fibers or fibrils. The filler may have any suitable particle size. In one embodiment of the invention, the filler may have a particle size of from 5nm to 10 μm, in some cases from 10nm to 5 μm, and in other cases from 25nm to 1 μm. When fillers are used, they can increase the tensile strength of the cured material.

Non-limiting examples of viscosity modifiers that may be used in the present invention include alkali-soluble, acid-soluble, and hydrophobically-modified alkali-soluble or acid-soluble emulsion polymers, those available under the trade name ACRYSOL from Rohm and Haas corporation^*Cellulose, modified cellulose, natural gums, such as xanthan gum, and the like.

Non-limiting examples of pigments useful in the present invention include silica, calcium carbonate, magnesium carbonate, titanium dioxide, iron oxide, and carbon black. The pigment may have any suitable particle size, and in one embodiment of the invention, the filler may have a particle size of 5nm to 10 μm, in some cases 10nm to 5 μm, and in other cases 25nm to 1 μm. When pigments are used, they can increase the tensile strength of the cured material.

Non-limiting examples of dyes that can be used in the present invention include mordant dyes, i.e., dyes prepared from plants, insects, and algae and direct dyes, non-limiting examples being those based on benzidine or biphenyl pair derivatives.

Non-limiting examples of ultraviolet UV absorbers useful in the present invention include benzotriazole-based UV absorbers, salicylate-based UV absorbers, benzophenone-based UV absorbers, hindered amine-based light stabilizers, and nickel-based light stabilizers.

Non-limiting examples of heat stabilizers useful in the present invention include HCl scavengers, one non-limiting example being epoxidized soybean oil, esters of beta-thiodipropionic acid, non-limiting examples being lauryl, stearyl, myristyl or tridecyl esters, mercaptobenzimidazole, zinc 2-mercaptobenzimidazole salt, zinc dibutyldithiocarbamate, dioctadecyl disulfide, pentaerythritol tetrakis- (. beta. -dodecylmercapto) propionate and lead phosphate.

Non-limiting examples of antioxidants useful in the present invention include 2, 6-di-tert-butylphenol, 2, 4-di-tert-butylphenol, 2, 6-di-tert-butyl-4-methylphenol, 2, 5-di-tert-butylhydroquinone, n-octadecyl-3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate, pentaerythritol-tetrakis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate]2,2 '-methylenebis (4-methyl-6-tert-butylphenol), 4' -butylidenebis (3-methyl-6-tert-butylphenol), 4 '-thiobis (3-methyl-6-tert-butylphenol), N' -diphenyl-p-phenylenediamine, 6-ethoxy-2, 2, 4-trimethyl-1, 2-dihydroquinoline and the product name IRGANOX from Ciba Specialty Chemicals, Basel, Switzerland^*The antioxidant product of (1).

In one embodiment of the present invention the two-component adhesive, sealant and/or coating composition of the present invention comprising component i) and component ii) is stable at 50 ℃. The term "stable" as used herein means that the composition does not gel or its viscosity reaches a point where it does not allow the composition to flow freely.

Embodiments of the present invention also relate to methods of applying the two-component adhesive, sealant and/or coating compositions described above comprising component i) and component ii). In these embodiments, the method comprises applying the mixture to one or more substrates.

One embodiment of the present invention is directed to a method of bonding a first substrate to a second substrate. The method comprises (a) combining component i) with component ii) to form a mixture, applying a coating of the mixture to at least one surface of a first substrate or a second substrate, and contacting one surface of the first substrate with one surface of the second substrate, wherein at least one contacting surface has the coating applied thereto.

Without being bound to a single theory, adhesion between substrates is achieved by using the compositions of the present invention, which is based on the interfacial reaction (e.g., wetting and surface energy) between the composition and the substrate and the development of cross-linking upon curing of the composition. In addition, the alkoxysilane functionality is selected to react with water at a rate low enough to allow mixing and use, yet fast enough to allow cure to be completed in a reasonable time. The definition of the alkoxysilane functions is listed in the detailed description of the X groups specified in formula I, which represent identical or different groups selected from C₁-C₁₀Straight or branched alkyl and C₁-C₁₀Straight or branched chain alkoxy, provided that at least two of the X groups present are alkoxy and that when one or both of the X groups are methoxy, at least one of the X groups must be C₁-C₁₀Straight or branched chain alkyl. The selection of "X" is effective to control the rate of cure.

In the present invention, one or both of the first substrate and the second substrate, or any additional substrate, may comprise wood, metal, plastic, paper, canvas, ceramic, stone, glass, concrete, and combinations thereof. The method of the present invention can be used to bond substrates containing the same or different materials.

In a particular embodiment, the metal comprises iron or aluminum. Furthermore, the plastic may be selected from the group consisting of polyethylene, polypropylene, polyethylene terephthalate and mixtures thereof. Further, the canvas may include one or more fibers selected from the group consisting of cotton fibers, nylon fibers, polyethylene fibers, polypropylene fibers, polyethylene terephthalate fibers, and mixtures thereof.

In one embodiment of the invention, the substrates are contacted at a temperature sufficient to promote adhesion of the composition thereto. Thus, the substrate is contacted at a temperature of at least 0 deg.C, in some cases at least 10 deg.C, in other cases at least 20 deg.C, and in some cases at least 25 deg.C. Moreover, the substrate may have a contact temperature of up to 150 ℃, in some cases up to 120 ℃, in other cases up to 100 ℃, and in some cases up to 80 ℃. The contact temperature of the substrate may be or vary between any of the values noted above.

In one embodiment of the invention, the substrates are contacted under pressure sufficient to promote adhesion of the composition thereto. Thus, the substrate is contacted at a pressure of at least ambient or atmospheric pressure, in some cases at least 10psi, in other cases at least 20psi, and in some cases at least 30 psi. Moreover, the substrate may have a contact temperature of up to 500psi, in some cases up to 400psi, in other cases up to 300psi, and in some cases up to 250 psi. The contact pressure of the substrate may be at or between any of the above-mentioned pressure values.

In one embodiment of the invention, the composition of the two-component composition, the contact temperature and the pressure of the substrate according to the invention, are such that the substrate is contacted for a sufficient period of time under conditions that will cause the composition to bond it together. Thus, the substrate is contacted for a period of at least 30 seconds, in some cases at least 1 minute, in other cases at least 5 minutes, and in some cases at least 15 minutes. Also, the substrate may be contacted for up to 24 hours, in some cases up to 12 hours, in other cases up to 8 hours, and in some cases up to 6 hours. The contact time of the substrate may be any length of time or may vary between any of the time values described above.

The invention also relates to an assembly manufactured according to the above method of bonding at least a first and a second substrate together.

Embodiments of the present invention provide a method of coating a substrate by applying the two-component composition described above to at least a portion of a surface of the substrate. The two-component composition can be used on any desired substrate, for example, wood, plastic, leather, paper, textiles, glass, ceramics, plaster, masonry, metal, and concrete. They can be applied by standard methods, for example, spraying, knife coating, pouring, casting, dipping and roll coating. The coating composition may be unpigmented or pigmented.

In one embodiment of the invention, the two-component composition is used to coat a metal substrate.

Coatings comprising the two-component composition are capable of curing at ambient or elevated temperatures. In one embodiment of the invention, the two-component composition cures at ambient temperature. In another embodiment, the curing process is heated to 60-120 deg.C, and in some cases 80-100 deg.C.

The two-component coating composition has a cure time of from 20 minutes to 30 days, in some cases from 20 minutes to 10 days, in other cases from 20 minutes to 24 hours, in some cases from 20 minutes to 12 hours, in other cases from 20 minutes to 6 hours, and in particular cases from 20 minutes to 4 hours, depending on the particular two-component composition and its cure temperature.

The present invention is described in more detail in the following examples, which are intended to be illustrative only, and various modifications and changes thereof will be apparent to those skilled in the art. All parts and percentages are by weight unless specifically limited.

Examples

Example 1

This embodiment demonstratesPreparation of the silane functional aspartate of the present invention. The aspartate resin can be prepared according to the method disclosed in Kramer et al, U.S. Pat. No. 4,364,955. To a 5 liter flask equipped with stirrer, thermocouple, nitrogen inlet, addition funnel and condenser was added 439.4g (1.99 equivalents (eq.)) of 3-aminopropylethoxysilane followed by 341.6g (1.99eq.) of diethyl maleate over 2 hours at 25 ℃ and incubated for 5 hours. The number of unsaturations, determined by iodine titration, was 0.6, indicating that the reaction was about 99% complete. The amine number was 140.6mg KOH/g resin. Brookfield engineering, Inc., Middleboro, Mass., under the trade name Brookfield at 25 deg.C, 100rpm^*The viscosity was 11cps as measured by a digital viscometer (model DV-II +, spindle 52).

Example 2

A comparative aspartate resin was prepared in the same manner as in example 1 except that 3-aminopropylethoxysilane was used in an amount of 356g (1.99 eq.).

Example 3

Preparation of Silane Terminated Polyurethane (STP) STP-1 according to the invention. To a2 liter round bottom flask equipped with stirrer, nitrogen inlet, heating unit, addition funnel and condenser was added 988g (0.18eq.) of ACCLAIM^*12200 (polyoxypropylene glycol, commercially available from Bayer Polymers LLC, Pittsburgh, Pa.). The flask was heated to 105 ℃ and vacuum was applied to 30 torr for 30min to remove the dissolved water. With the vacuum released and the flask cooled to 30 ℃, 32g (0.36eq.) of Toluene Diisocyanate (TDI) was added thereto. The mixture was heated to 60 ℃ and held for 36 hours, after which the NCO content, determined by NCO titration, was 0.75% by weight (theoretical value 0.74%). 72.15g (0.181eq.) of the silane-functional aspartate obtained in example 1 were then added and the mixture was heated to 60 ℃ and held for 1 hour. No NCO content was found by IR. Followed by the addition of 5.5g of moisture scavenger vinyltrimethoxysilane. The viscosity at 25 ℃ was 31,500cps and the density was 8.4 Ibs/gal.

Example 4

Comparative example preparation of Silane Terminated Polyurethane (STP) STP-2. To a 5 liter round bottom flask equipped with stirrer, nitrogen inlet, heating unit, addition funnel and condenser was added 2,700g (0.49eq.) of ACCLAIM^*12200. The flask was heated to 105 ℃ and vacuum was applied to 30 torr for 30min to remove the dissolved water. With the vacuum released and the flask cooled to 30 ℃, 110.3g (0.36eq.) of isophorone diisocyanate (IPDI) was added thereto. The mixture was heated to 60 ℃ and held for 36 hours, after which the NCO content, determined by NCO titration, was 0.64% by weight (theoretical value 0.74%). 181.6g (0.49eq.) of the silane-functional aspartate obtained in example 2 are then added and the mixture is heated to 60 ℃ and held for 15 hours. No NCO content was found by IR. Followed by the addition of 5.5g of moisture scavenger vinyltrimethoxysilane. The viscosity at 25 ℃ was 72,200cps and the density was 8.4 Ibs./gal.

Example 5

Stability testing of STP samples. 50g of each sample and 0.5g were mixed and stored at 23 ℃ and 50 ℃ respectively. The viscosity is used under the trade name Brookfield^*The digital viscometer (model DV-I +, LV shaft #4) at 12rpm, at 23 ℃ and 50 ℃ respectively. The results are shown in the table below, with all items being viscosity in cps.

Condition	STP-1@23℃	STP-1@50℃	STP-2@23℃	STP-2@50℃
					Time of sample storage
Initially, the process is started	31,500	-	72,200	-
					2 days	31,600	7,650	130,800	Gelling
7 days	34,350	9,850	Gelling	Gelling

These data demonstrate the excellent stability and shelf life of the compositions of the present invention.

Example 6

This example demonstrates the cure rate of STP-1. By mixing 100g STP-1, 1g of SILQUEST commercially available from OSispecialties, Inc. Danbury CT under the trade name of SILQUEST^*Diaminosilane A-1120, 2g commercially available from OSi Specialties under the trade name SILQUEST^*An organofunctional silane of A-171, and 1g of a compound commercially available from Rohm and Haas Inc., Philadelphia, PA under the trade name METATIN^*740 bisDi- (n-butyl) tin ketonate produces a single component system. The curing speed was determined as described in Pacific Scientific instruments Nuttaals DG-9600 and DG-9300 by using a 45mil wet film on a Gardner Dry Time Meter (BYK-Gardner USA, Columbia, Md.). The Dry TimeMeter has a needle that passes through the wet film. When the needles were higher than the semi-cured film, the surface was considered to have reached dryness. At this level of cure, the needle still leaves a mark. When the surface had no die-face scar, it was determined that full cure had been achieved. At room temperature, surface drying took 4.25 hours and complete curing took 11.75 hours.

Example 7

This example demonstrates the formation of a two-part adhesive. The component A is prepared by using a tin catalyst, and the component B is prepared by using water.

Pigmenting the formulation without pigments

Component A

STP1 50.0 50.0

Carbon black¹ 25.0

Diisodecyl phthalate 10.025.0

Silquest A-1120 0.5 0.5

Silquest A-171 0.25 0.25

Bis- (n-butyl) tin diketonates² 0.5 0.5

¹MONARCH^*120 available from Cabot Corporation, Billerica, MassAnd is a registered trademark of Cabot.

²METATIN^*740 is available from Rohm and Haas inc, philiadelphia, PA, and is a registered trademark of Rohmand Haas.

Component B

STP-1 50.0 50.0

Carbon black¹ 25.0

Diisodecyl phthalate 10.025.0

Deionized water 1.00.5

¹MONARCH^*120 is available from Cabot Corporation, Billerica, MA and is a registered trademark of Cabot.

Components A and B were prepared by passing the mixture through a Hauschild SPEEDMIXER available from Flack Inc., Landrum, SC^TMMix for 1 minute each. When used, component a and component B were mixed for evaluation. Mixing the mixture in a TEFLON^*(registered trademark of E.I. du Pont DE Nemours and Company, Wilmington, DE) plates were wetted and stretched 50 mils to produce films which were cured at 72F (22℃), 50% RH for 1 week. Tensile, elongation at break, and modulus were measured on a 0.5 inch butterfly crack specimen using a motor universal tester from Instron Corp, Canton, MA. at a crosshead speed of 20.0 inches/minute (7.9 cm/min). The drying time was determined as described above.

Drying time

Surface drying (hours) 2.42.1

Hard dry (hours) 8.58.5

Tensile Properties

Elongation,% 133157

Tensile Strength (psi) 86315

100% modulus 71179

Tear Strength (pli) 720

The above examples demonstrate that the cure speed of the two-component formulation is faster than the one-component formulation; moreover, the dyeing improves the tensile properties of the composition.

Although the present invention has been described in detail hereinabove for the purpose of illustration, it is to be understood that this is by way of illustration only and that variations can be made by those skilled in the art without departing from the spirit and scope of the invention except as it may be limited by the claims.

Claims (28)

1. A two-part adhesive, sealant or coating composition comprising an alkoxysilane-functional urethane comprising the reaction product of a) and b)

a) A reaction product of a hydroxy-functional compound and a polyisocyanate, the reaction product containing isocyanate functional groups; and

b) a compound of formula I:

wherein the content of the first and second substances,

x represents the same or different and is selected from C₁-C₁₀Straight or branched alkyl and C₁-C₁₀Straight or branched chain alkoxy, provided that at least two X are alkoxy, and if one or both X groups are methoxy, at least one X group must be C₁-C₁₀A linear or branched alkyl group,

y represents C₁-C₈A linear or branched alkylene group, which may be substituted,

R₂and R₅Are identical or different and represent organic radicals which are inert to isocyanate groups at temperatures of 100 ℃ or less, and

R₃and R₄Are identical or different and represent hydrogen or an organic group which is inert towards isocyanate groups at temperatures of 100 ℃ or less,

wherein the two-component composition comprises

(i) A first component comprising a portion of an alkoxysilane-functional urethane and water; and

(ii) a second component comprising a remaining portion of the alkoxysilane-functional urethane and a catalyst.

2. The composition of claim 1 wherein the hydroxy-functional compound in a) is a polyol.

3. The composition of claim 1 wherein the hydroxy-functional compound in a) is a diol.

4. The composition of claim 1 wherein the hydroxy-functional compound is selected from the group consisting of polyester monols, diols, polyols and mixtures thereof, (meth) acrylic monols, diols, polyols and mixtures thereof, polyether monols, diols, polyols and mixtures thereof, hydrocarbon monols, diols, polyols and mixtures thereof.

5. The composition of claim 1, wherein the compound of formula I is the reaction product of an N- (trialkoxysilylalkyl) amine and a dialkyl maleate.

6. The composition of claim 5, wherein the N- (trialkoxysilylalkyl) amine has a structure represented by formula (II):

NH₂-R¹-Si(-O-R⁶)₃ (II)

wherein R is¹Is C₁-C₈A linear or branched alkylene group; r⁶Independently selected from C₂-C₁₀Straight or branched chain alkyl.

7. The composition of claim 1, wherein the polyisocyanate contains 2 to 6 isocyanate groups.

8. The composition of claim 1, wherein the polyisocyanate has the structure shown in formula (III):

OCN-R⁷-NCO (III)

wherein R is⁷Is selected from C₂-C₂₄Linear, branched and cyclic alkylene, arylene and aralkylene groups, which may optionally contain one or more isocyanate groups.

9. The composition of claim 1 wherein the polyisocyanate is selected from the group consisting of 1, 4-tetramethylene diisocyanate, 1, 6-hexamethylene diisocyanate, 2, 4, 4-trimethyl-1, 6-hexamethylene diisocyanate, 1, 12-dodecamethylene diisocyanate, cyclohexane-1, 3-and-1, 4-diisocyanate, 1-isocyanato-2-isocyanatomethylcyclopentane, 1-isocyanato-3-isocyanatomethyl-3, 5, 5-trimethyl-cyclohexane, bis- (4-isocyanatocyclohexyl) methane, 2, 4' -dicyclohexylmethane diisocyanate, 1, 3-and 1, 4-bis- (isocyanatomethyl) cyclohexane, bis- (-4-isocyanato-3-methylcyclohexyl) methane, α, α, α ', α' -tetramethyl-1, 3-diisocyanate, α, α ', α' -1, 4-xylylene diisocyanate, 1-isocyanato-1-methyl-4 (3) -isocyanatomethylcyclohexane, 2, 4-hexahydrotolylene diisocyanate, 2, 6-hexahydrotolylene diisocyanate, 1, 3-phenylene diisocyanate, 1, 4-phenylene diisocyanate, 2, 4-tolylene diisocyanate, 2, 6-tolylene diisocyanate, 2, 4-diphenylmethane diisocyanate, 4 '-diphenylmethane diisocyanate, 4, 3' -diphenylmethane diisocyanate, mixtures thereof, and mixtures thereof, 1, 5-diisocyanato naphthalene and mixtures thereof.

10. The composition of claim 1 further comprising in one or both of component i) and component ii) one or more materials selected from the group consisting of leveling agents, wetting agents, flow control agents, anti-skinning agents, anti-foaming agents, fillers, adhesion promoters, viscosity modifiers, plasticizers, pigments, dyes, UV absorbers, thermal stabilizers, antioxidants and mixtures thereof.

11. The composition of claim 1, wherein the reactive silane groups of the compound of formula I are introduced as a reaction product of an isocyanate group and an-NH-group of formula I.

12. The composition of claim 1 wherein the catalyst in ii) is one or more selected from the group consisting of p-toluenesulfonic acid, dibutyltin dilaurate, dibutyltin acetoacetate, triethylamine and triethylenediamine.

13. The composition of claim 1 wherein component i) and component ii) are stable at 50 ℃.

14. The composition of claim 1 wherein the equivalent ratio of hydroxyl groups in the hydroxyl functional compound to isocyanate groups in the polyisocyanate in a) is from 1: 10 to 1: 1.

15. The composition of claim 1 wherein the reaction product a) is 50 to 99 weight percent of the alkoxysilane functional carbamate and the amine functional aspartate b) is 1 to 5 weight percent of the alkoxysilane functional carbamate.

16. The composition of claim 1 wherein component i) comprises 10 to 90 wt% and component ii) comprises 10 to 90 wt% of the composition.

17. The composition of claim 4 wherein the polyether has a number average molecular weight of 500-15,000.

18. A method of applying a composition to a substrate comprising mixing component i) and component ii) of claim 1.

19. A method of bonding a first substrate to a second substrate, the method comprising

Combining component i) and component ii) of claim 1 to form a mixture,

applying a coating of the mixture to at least one surface of the first substrate or the second substrate, and

contacting one surface of a first substrate with one surface of a second substrate, wherein at least one contacting surface has a coating applied thereto.

20. The method of claim 19, wherein one or both of the first substrate and the second substrate comprises a substrate selected from the group consisting of wood, metal, plastic, paper, canvas, ceramic, stone, glass, and concrete.

21. The method of claim 20, wherein the metal comprises iron or aluminum.

22. The method of claim 20 wherein the plastic is selected from the group consisting of polyethylene, polypropylene, polyethylene terephthalate, and mixtures thereof.

23. The method of claim 20, wherein the canvas comprises one or more fibers selected from the group consisting of cotton fibers, nylon fibers, polyethylene fibers, polypropylene fibers, polyethylene terephthalate fibers, and mixtures thereof.

24. The method of claim 19, wherein the first substrate and the second substrate are contacted at a temperature of from 0 ℃ to 150 ℃.

25. The method of claim 19, wherein the first substrate and the second substrate are contacted under pressure conditions from atmospheric pressure to 500 psi.

26. An assembly prepared according to the method of claim 19, comprising at least a first substrate and a second substrate bonded together.

27. A method of coating a substrate comprising applying the composition of claim 1 to at least a portion of a surface of a substrate.

28. A coated substrate prepared according to the method of claim 27.